Acceptorless dehydrogenative condensation of o-aminobenzamides with aldehydes to quinazolinones in water catalyzed by a water-soluble iridium complex [Cp*Ir(H2O)3][OTf]2
作者： Feng Li , Lei Lu , Juan Ma
DOI: 10.1039/C5QO00255A
关键词:
摘要: A general and efficient method for the synthesis of quinazolinones via acceptorless dehydrogenative condensation o-aminobenzamides with aldehydes in water has been accomplished. In presence [Cp*Ir(H2O)3][OTf]2, a variety desirable products were obtained high yields atom economy under environmentally benign conditions. Notably, this research will facilitate progress reactions catalyzed by water-soluble organometallic complexes.
rsc.org
sci-hub.se 参考文章(78)
TAKUZO HISANO, MASATAKA ICHIKAWA, AKIRA NAKAGAWA, MASAYOSHI TSUJI, Studies on organosulfur compounds. XII. Syntheses and pharmacological activities of 2-heterocyclic substituted 4(3H)-quinazolinones. Chemical & Pharmaceutical Bulletin. ,vol. 23, pp. 1910- 1916 ,(1975) , 10.1248/CPB.23.1910
Lei Lu, Juan Ma, Panpan Qu, Feng Li, Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(N-alkyl)benzenesulfonamides via Iridium-Catalyzed N-Alkylation with Alcohols Organic Letters. ,vol. 17, pp. 2350- 2353 ,(2015) , 10.1021/ACS.ORGLETT.5B00824
Yiliang Zhang, Matthew R. Sheets, Erum K. Raja, Kenneth N. Boblak, Douglas A. Klumpp, Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: mechanisms correlated to charge distributions. Journal of the American Chemical Society. ,vol. 133, pp. 8467- 8469 ,(2011) , 10.1021/JA202557Z
Nigel J. Liverton, Donna J. Armstrong, David A. Claremon, David C. Remy, John J. Baldvin, Robert J. Lynch, Guixiang Zhang, Robert J. Gould, Nonpeptide glycoprotein IIb/IIIa inhibitors: substituted quinazolinediones and quinazolinones as potent fibrinogen receptor antagonists. Bioorganic & Medicinal Chemistry Letters. ,vol. 8, pp. 483- 486 ,(1998) , 10.1016/S0960-894X(98)00047-X
Seiji Ogo, Nobuyuki Makihara, Yoshihito Watanabe, pH-Dependent Transfer Hydrogenation of Water-Soluble Carbonyl Compounds with [Cp*IrIII(H2O)3]2+ (Cp* = η5-C5Me5) as a Catalyst Precursor and HCOONa as a Hydrogen Donor in Water Organometallics. ,vol. 18, pp. 5470- 5474 ,(1999) , 10.1021/OM9903689
Naveen Mulakayala, Bhaskar Kandagatla, Ismail, Rajesh Kumar Rapolu, Pallavi Rao, Chaitanya Mulakayala, Chitta Suresh Kumar, Javed Iqbal, Srinivas Oruganti, InCl3-catalysed synthesis of 2-aryl quinazolin-4(3H)-ones and 5-aryl pyrazolo[4,3-d]pyrimidin-7(6H)-ones and their evaluation as potential anticancer agents. Bioorganic & Medicinal Chemistry Letters. ,vol. 22, pp. 5063- 5066 ,(2012) , 10.1016/J.BMCL.2012.06.003
Ken-ichi Fujita, Tetsuya Yoshida, Yoichiro Imori, Ryohei Yamaguchi, Dehydrogenative Oxidation of Primary and Secondary Alcohols Catalyzed by a Cp*Ir Complex Having a Functional C,N-Chelate Ligand Organic Letters. ,vol. 13, pp. 2278- 2281 ,(2011) , 10.1021/OL2005424
C. Gunanathan, D. Milstein, Applications of acceptorless dehydrogenation and related transformations in chemical synthesis. Science. ,vol. 341, pp. 1229712- 1229712 ,(2013) , 10.1126/SCIENCE.1229712
Raymond Ziessel, Efficient homogeneous photochemical water gas shift reaction catalysed under extremely mild conditions by novel iridium(III) complexes: [(η5-Me5C5)Ir(bpy)Cl]+, [(η5-Me5C5)Ir(bpy)H]+, and [(η5-Me5C5)Ir(phen)Cl]+(bpy = 2,2′-bipyridine; phen = 1,10-phenanthroline) J. Chem. Soc., Chem. Commun.. ,vol. 0, pp. 16- 17 ,(1988) , 10.1039/C39880000016
Feng Li, Juan Ma, Lei Lu, Xiaofeng Bao, Wanying Tang, Combination of gold and iridium catalysts for the synthesis of N-alkylated amides from nitriles and alcohols Catalysis Science & Technology. ,vol. 5, pp. 1953- 1960 ,(2015) , 10.1039/C4CY01506A